Careers

Who we are

At Sixfold, we’re building the AI platform that transforms how insurers evaluate and price risk. Not just another tool that generates summaries or flags issues—we’re creating AI agents that actually understand risk the way veteran underwriters do. Our platform is processing billions in premium for some of the world’s largest carriers, and we’re just getting started.

The technical challenges are wild. We’re teaching AI to understand that a bakery in Florida faces different risks than one in Montana. To know when a manufacturing company’s pivot from toys to medical devices fundamentally changes their risk profile. To make million-dollar decisions with the same intuition as someone who’s been underwriting for 20 years.

What makes Sixfold special isn’t just the technology—it’s that we’re building it with people who deeply understand insurance. Our team includes folks who’ve built and scaled carriers, researchers who’ve pushed the boundaries of AI, and engineers who just love solving seemingly impossible problems.

We’re still early, but the impact is already real. If you want to build AI that matters—that affects real businesses, real people, and billions in economic activity—Sixfold is where you should be. We’re not just digitizing insurance. We’re reimagining what it can be.

The Role

We're looking for a talented Product Designer to join our team. This role is ideal for a generalist designer who thrives in a collaborative, agile environment and enjoys tackling complex problems in enterprise AI software. You'll work closely with PMs, developers, and AI engineers, contributing to an experience that blends automation with the nuanced needs of our users. You'll help design our flagship product and its key features, shaping the future of underwriting. As the fourth designer at the company, you will also have the opportunity to shape our design processes and culture, establish design patterns, and play a key role in defining how design evolves within our organization.

What You'll Do

• Contribute to our Property & Casualty underwriting product features end-to-end, from discovery through to implementation and iteration based on feedback.
  • This could be a small adjustment to improve the human-in-the-loop experience, adjustments to AI workflows to optimize outputs for users, or green field projects that represent a whole new level of analysis for the insurance industry.
• Contribute to product strategy by leveraging detailed user research to inform product direction.
• Collaborate closely with PMs, developers, and AI engineers to create exceptional user-centered designs.
• Jam with the design team on new designs, the design system, agentic prototyping harnesses and anything else that enables Sixfold designers to excel. Contribute to and grow our design system to ensure a consistent and delightful user experience.
• Dig into data, synthesize patterns, and translate those patterns to prompts and engineers. Design meticulously well-written LLM outputs and copy to create intuitive UI and API experiences.
• Facilitate team workshops to help find the best solutions. Navigate ambiguity and proactively find ways to simplify complex workflows, ensuring a seamless user experience.
• Help our customers smoothly transition to the world of enterprise AI agents.

What We're Looking For

• 2+ years of experience: Proven track record as a product designer, ideally with experience in enterprise software. A portfolio demonstrating outcomes that were fully delivered into production. We're open to non-traditional backgrounds for candidates with strong AI-native product experience.
• Generalist mindset: Experience across the design process, from user research to visual design.
• AI-native builder: You've designed AI-first products—not just added AI features to existing workflows. You understand the unique challenges of designing for probabilistic systems, from handling uncertainty to crafting human-AI handoffs.
• Tinkerer mentality: When you see an inefficiency, you build something to fix it rather than waiting for someone else. You prototype with AI tools, stay current on new capabilities, and experiment because you're genuinely curious—not because it's your job.
• Specialized depth: We're looking for someone with meaningful experience in at least one of these areas: UX writing/content design, human-in-the-loop AI systems, or API design. Systems thinker: Ability to see the bigger picture and understand how design decisions impact the overall product experience.
• Adaptability: Ability to handle ambiguity and take ownership of finding solutions that simplify complex workflows.
• Collaborative first: Desire to work in an environment that values close collaboration, rapid iteration, and shared ownership of outcomes.
• Growth mindset: Once you're here, you'll get to stay up-to-date and design with the latest AI techniques.
• Enterprise SaaS / Insurtech experience (preferred): Familiarity with designing for complex, data-driven workflows. Even better if you've worked in insurance before.

You'll be a great fit if…

• You enjoy parsing complex systems and finding the best way to solve a problem—whether it's in the UI, through an AI workflow, or with a multi-agent system.
• You thrive on close collaboration with PMs, engineers, AI researchers, and customers.
• You can maintain a big-picture perspective while diving deep into the data to drive decisions.
• You're excited about building at the cutting edge of AI and discovering new UX patterns where best practices haven't been solidified.
• You have an itch to solve problems you see, even if it's not directly in your purview.
• You want to rethink what a good design process looks like in the world of AI.
• You've built your own tools, automations, or prototypes to solve problems—and you'd do it again tomorrow if you spotted a new opportunity.
• You follow AI developments because you find them genuinely interesting, and you've probably tried out a new model or tool in the last month just to see what it can do.

Additional Information:

• Expected full-time salary range between $120,000 to $150,000 + equity + benefits.
• Advertised and actual salary ranges may differ by geographic area, work experience, education, and/or skill level.
• About half the company works in the NYC office 3-4 days a week. This can be a remote role, but applicants need to work no more +/- 3 hours from Eastern time.
• This position does not include visa sponsorship. Candidates must be authorized to work in the United States without requiring employer sponsorship.

Our Commitment:

We foster an environment that welcomes professionals with a diversity of backgrounds and ideas. We value passionate professionals who bring creativity, determination, and a commitment to our mission. At Sixfold, every team member plays a crucial role, with opportunities to make meaningful and visible contributions to our success.

We believe in empowering our employees through continuous growth, learning, and a proactive problem-solving approach. Our comprehensive compensation package includes competitive salaries, equity opportunities, and robust benefits, all within a supportive and inclusive workplace culture. If you're driven to make a significant impact alongside exceptional colleagues, we want to hear from you.

We are committed to accessibility and provide reasonable accommodations for qualified individuals with disabilities and disabled veterans throughout our recruitment process.If you have any difficulty using our online system and you need accommodation due to a disability, please reach out to us directly at (646) 847-8824.

Sixfold does not accept unsolicited agency resumes and is not responsible for any fees related to unsolicited resumes.